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A kind of method for preparing n-heterocyclic compound

A technology of compound and condensation reaction, which is applied in the preparation of compounds and their intermediates, and the preparation of N-heterocyclic compounds, which can solve the problems of complex preparation methods

Active Publication Date: 2020-12-22
SUNSHINE LAKE PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The Suvorexant structure contains a seven-membered diazoheterocyclic ring and chiral carbon. During its preparation, it is necessary to form a ring and construct a chiral carbon or to split to obtain a single-configuration target compound; the preparation method in the prior art is comparatively Complex, need to study a simplified preparation method suitable for industrialization

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  • A kind of method for preparing n-heterocyclic compound
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  • A kind of method for preparing n-heterocyclic compound

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specific Embodiment approach

[0037] In order to enable those skilled in the art to better understand the technical solutions of the present invention, some non-limiting examples are further disclosed below to further describe the present invention in detail.

[0038] The reagents used in the present invention can be purchased from the market or can be prepared by the methods described in the present invention.

[0039] In the present invention, Boc means tert-butoxycarbonyl, Et means ethyl, g means gram, mL means milliliter, and mol / L means mole / liter.

Embodiment 1

[0040] Example 1 Preparation of N-tert-butoxycarbonyl-N'-(4-methoxybenzyl)ethylenediamine

[0041] Add p-methoxybenzaldehyde (13.6g, 100mmol) and ethanol (272mL) successively to the reaction flask, N-boc ethylenediamine (16g, 100mmol) was stirred at room temperature for 24 hours, the system was cooled to 0°C, and then separated Sodium borohydride (5.67 g, 150 mmol) was added in 4 batches, and the addition was completed in 30 minutes. After the addition was completed, the mixture was incubated and stirred for 30 minutes, then warmed to room temperature and stirred for 2 hours. Add 6mol / L hydrochloric acid at room temperature to quench the system until the system becomes acidic (pH=2-6). After stirring for 30 minutes, add sodium hydroxide to adjust the system to alkalinity, and then concentrate under reduced pressure at 60°C to remove ethanol. Add 200 mL each of water and methylene chloride, separate the organic phase, extract the aqueous phase once with methylene chloride, and ...

Embodiment 2

[0042] Embodiment 2 prepares compound (07)

[0043]

[0044] In the reaction flask, add N-tert-butoxycarbonyl-N'-(4-methoxybenzyl)ethylenediamine (24g, 85.7mmol) and dichloromethane (240mL) successively, and 10mol / L sodium hydroxide ( 21.3mL), stirred at room temperature. Then, 4-chloro-2-butanone (11.8 g, 111.4 mmol) was slowly added dropwise, stirred at room temperature, and the system changed from clear to orange-yellow. After 14 hours, 4-chloro-2-butanone (4.5 g, 42.8 mmol) was added to the reaction system, and the stirring reaction was continued for 4 hours. Then add 240mL of water to the reaction system, separate the organic phase, extract the aqueous phase once with 180mL of dichloromethane, and concentrate the combined organic phase at 50°C under reduced pressure to obtain [2-((4-methoxybenzyl)(3- Oxobutyl) amino) ethyl] tert-butyl formate, compound (07): 30 g of reddish-brown oil, HPLC purity 99%.

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Abstract

The invention provides a method for preparing an N-heterocyclic compound and belongs to the technical field of pharmacy. The method for preparing the N-heterocyclic compound comprises the steps of carrying out condensation reaction on an N-heterocyclic intermediate compound and 2-ethoxy-5-chlorobenzoxazole under an acid condition, and carrying out aftertreatment to prepare the compound (1). The method is simple and convenient, and can be applied to industrial production.

Description

technical field [0001] The invention relates to a method for preparing N-heterocyclic compounds, in particular to a method for preparing a compound containing a seven-membered nitrogen heterocycle and an intermediate thereof, and is used in the field of pharmaceutical technology. Background technique [0002] Suvorexant (trade name Belsomra) is an orexin (orexin) receptor antagonist that can affect the signal transduction of the orexin pathway and is clinically used to treat diseases such as insomnia; its structure is shown in the following formula (1): [0003] [0004] The Suvorexant structure contains a seven-membered diazoheterocyclic ring and chiral carbon. During its preparation, it is necessary to form a ring and construct a chiral carbon or to split to obtain a single-configuration target compound; the preparation method in the prior art is comparatively Complicated, it is necessary to study a simplified preparation method suitable for industrialization. Content...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D413/14
CPCC07D413/14
Inventor 何必飞刘光元樊玉平王仲清罗忠华
Owner SUNSHINE LAKE PHARM CO LTD
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